Hydrochloric Acid → 7-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid

HRID 1154811Notes

Reaction equation

HRID 1154811 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C.[CH3:21][O:22][N:23]=[C:24]([C:41](=[O:43])[CH3:42])[C:25]([NH:27][CH:28]1[C:39](=[O:40])[N:30]2[CH:31]([C:36]([OH:38])=[O:37])[CH:32](O)[CH2:33][S:34][C@H:29]12)=[O:26].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:21][O:22][N:23]=[C:24]([C:41](=[O:43])[CH3:42])[C:25]([NH:27][CH:28]1[C:39](=[O:40])[N:30]2[C:31]([C:36]([OH:38])=[O:37])=[CH:32][CH2:33][S:34][C@H:29]12)=[O:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 867380887-(2-Methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125287-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acidYield 69.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroaceticanhydride (0.2 ml.) and triethylamine (0.12 ml.) were added to a solution of 7-(2-methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 100 mg.) in dry tetrahydrofuran (10 ml.), and allowed to stand at room temperature for 10 minutes. Ethyl acetate (30 ml.) and water (10 ml.) were added to the reaction mixture and adjusted to pH 2 with hydrochloric acid. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and then evaporated in vacuo. The residue was crystallized with diethyl ether to give 7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 66 mg.).

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized with diethyl ether

Sources & evidence

ORD record
ord-9a165a8cd3e8416c9cae0a611e4fca35
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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